JPH11228951A - Organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an org. electroluminescent element having a high luminance and excellent luminescent characteristics by forming at least one org. thin film layer comprising a trianthrylene compd. between an anode and a cathode. SOLUTION: A trianthrylene compd. of the formula is used for forming an org. thin film layer of an org. electroluminescent element. In the formula, R<1> to R<26> are each H, halogen, hydroxyl, amino, alkyl, an arom. hydrocarbon group, carboxyl, or the like provided two of them may combine with each other to form a ring. The compd. has high carrier transport properties and can form a hole transport layer or an electron transport layer. An EL element prepd. by using the compd. having diarylamino groups as a luminescent material, a hole transport material, or an electron transport material emits light with an esp. high luminance. An org. EL element includes a luminescent layer, a hole transport layer, and an electron transport layer formed between an anode and a cathode, and the compd. may be used as any one of these org. layers or may be used as a mixture in which the compd. is present as a dopant.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device, and more particularly, to an organic electroluminescence device having excellent light emission characteristics.

[0002]

2. Description of the Related Art Organic electroluminescence (EL)
The device is a device having a structure in which a light emitting layer is sandwiched between an anode and a cathode. An electric field is applied to recombine holes injected from the anode with electrons injected from the cathode. This is a self-luminous element utilizing the principle that a fluorescent substance in a light emitting layer emits light by energy. A low-voltage driven organic EL device having a laminated structure using tris (8-hydroxyquinolinol aluminum) as a light emitting layer and a triphenyldiamine derivative as a hole transport layer has been described by Eastman Kodak Co., Ltd. W. Tang et al. W. Tang, S .;
A. VanSlyke, Applied Physics Letters
s), vol. 51, p. 913, 1987 and the like, research on organic EL devices having a laminated structure using an organic material as a constituent material has been actively conducted.

[0003] Advantages of the laminated structure include an improvement in the efficiency of injecting holes into the light emitting layer, and an improvement in the efficiency of generation of excitons generated by blocking and recombining electrons injected from the cathode. And confinement of excitons generated in the light emitting layer to improve luminous efficiency. Therefore, the organic EL device has a two-layer type of a hole transporting (injection) layer and an electron transporting light emitting layer, or a three-layer type of a hole transporting (injection) layer, a light emitting layer, and an electron transporting (injection) layer. Many have a structure. Further, in the organic EL device having the laminated structure, various ideas have been devised on the laminated structure and the method of forming the laminated structure in order to increase the recombination efficiency of injected holes and electrons.

As the hole transporting material, for example, JP-A-8-20771, JP-A-8-40995,
JP-A-8-40997, JP-A-8-5433
No. 97, JP-A-8-87122 and the like, 4,4 ′,
4 "-tris (3-methylphenylphenylamino) triphenylamine or N, N'-diphenyl-N, N'-
Triphenylamine derivatives such as bis (3-methylphenyl)-[1,1'-biphenyl] -4,4'-diamine and aromatic diamine derivatives are well known. Oxadiazole derivatives, triazole derivatives and the like are well known as electron transporting materials. Examples of the luminescent material include tris (8-quinolinolate) aluminum complex, as reported in JP-A-8-239655, JP-A-7-138561, JP-A-3-200289, and the like. Light-emitting materials such as a chelate complex, a coumarin derivative, a tetraphenylbutadiene derivative, a bisstyrylarylene derivative, and an oxadiazole derivative are known. Furthermore, it has been reported that the use of these light-emitting materials enables light emission in the visible region from blue to red to be obtained, and realization of a color display element is expected.

[0005]

However, as described in the above-mentioned publication, although high-luminance and long-life organic EL devices are disclosed or reported, they cannot be said to be sufficient for practical use yet. That is the fact. Therefore, there is a strong demand for developing a high-performance material and realizing an organic electroluminescence device having high luminance and excellent light emission characteristics. In view of the circumstances as described above, an object of the present invention is to provide an organic electroluminescent device having high luminance and excellent light emitting characteristics.

[0006]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that an organic EL device manufactured using a specific trianthrylene compound as a light emitting material.
The device has been found to emit light with higher luminance than the conventional organic EL device, and furthermore, since the specific trianthrylene compound has a high carrier transporting property, it is used as a material for forming a hole transporting layer, or The present inventors have found that an organic EL device that emits light with higher luminance than conventional organic EL devices can be manufactured by using the material for forming the electron transport layer, and have completed the present invention. Further, among trianthrylene compounds, an organic EL element using a compound having a diarylamino group as a substituent as a light-emitting material, a hole-transport material, or an electron-transport material can emit light with particularly high luminance. Thus, the present invention has been completed. Further, among the trianthrylene compounds having a diarylamino group as a substituent, an organic EL device manufactured using a compound in which an aryl group has a styryl group as a substituent is used as a light-emitting material, a hole-transport material, or an electron-transport material. The present inventors have found that light emission with particularly high luminance can be obtained, and have completed the present invention.

That is, the present invention relates to an organic electroluminescent device having one or more organic thin film layers including a light emitting layer between an anode and a cathode, wherein at least one layer comprises a material represented by the following general formula (1) singly or as a mixture. An organic electroluminescence device characterized by including as:

Embedded image (Wherein, R ^{1 to} R ²⁶ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted Alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group , A substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, and a carboxyl group, and two of R ^{1 to} R ²⁶ may form a ring.) The present invention relates to an organic electroluminescent device having one or more organic thin film layers including a light emitting layer between an anode and a cathode, At least one of the organic thin-film layers is an organic electroluminescent device characterized by containing the material represented by the following general formula (2) alone or as a mixture.

Embedded image (Wherein, R ^{1 to} R ²⁶ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted Alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group Or a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group, and two of R ^{1 to} R ²⁶ may form a ring. R
¹ at least one of to R ²⁶ are -NAr ¹ Ar ² (A
r ¹ and Ar ² each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. ) Is a diarylamino group. The present invention also relates to an organic electroluminescence device having one or more organic thin film layers including a light emitting layer between an anode and a cathode, wherein at least one of the organic thin film layers comprises a compound represented by the general formula (2). An organic electroluminescent device, wherein at least one of Ar ¹ and Ar ² in at least one —NAr ¹ Ar ² group contains, alone or as a mixture, a material having a styryl group as a substituent. Further, the present invention provides an organic electroluminescent device comprising at least a hole transport layer as the organic thin film layer, wherein the layer contains the compound represented by the general formula (1) alone or as a mixture. It is. Further, the present invention provides an organic electroluminescence device comprising at least a hole transport layer as the organic thin film layer, wherein this layer contains the compound represented by the general formula (2) alone or as a mixture. It is. Further, the present invention, the organic thin film layer has at least a hole transporting layer, among the layers of the compound represented by the general formula (2), at least one -NAr ¹ Ar
At least one of Ar ^1, Ar ² groups in the ² group is an organic electroluminescence element which comprises a material having a styryl group as a substituent alone or as a mixture. Further, the present invention is an organic electroluminescence device having at least an electron transport layer as the organic thin film layer, wherein this layer contains the compound represented by the general formula (1) alone or as a mixture. . Further, the present invention is an organic electroluminescence device having at least an electron transport layer as the organic thin film layer, wherein this layer contains the compound represented by the general formula (1) alone or as a mixture. . Further, the present invention, the organic thin film layer has at least an electron transport layer, among the layers of the compound represented by the general formula (2), Ar ¹ in at least one -NAr ¹ Ar ² group, Ar ²
An organic electroluminescent device comprising a material in which at least one of the groups has a styryl group as a substituent, alone or as a mixture.

The compound specified in the present invention as a material forming at least one layer of the light emitting layer or the laminated film is a compound having a structure represented by the general formula (1). R ^{1 to} R
²⁶ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted Cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy Group,
Represents a substituted or unsubstituted alkoxycarbonyl group or a carboxyl group. R ^{1 to} R ²⁶ are two of them.
Together may form a ring.

The halogen atom includes fluorine, chlorine, bromine and iodine. The substituted or unsubstituted amino group is represented by —NX ¹ X ² , wherein X ¹ and X ² are each independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and a s. -Butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2- Hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3
-Trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t- Butyl group,
1,2,3-trichloropropyl group, chloromethyl group,
1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloro Propyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3
-Dibromoisopropyl group, 2,3-dibromo t-butyl group, 1,2,3-tribromopropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-
Bromoisobutyl group, 1,2-dibromoethyl group, 1,
3-dibromoisopropyl group, 2,3-dibromo t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group,
-Iodoisobutyl group, 1,2-diiodoethyl group,
1,3-diiodoisopropyl group, 2,3-diiodo t
-Butyl group, 1,2,3-triiodopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo t-butyl group, 1,2,3-triiodopropyl group,
Aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino t-butyl group, 2,3-triaminopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3 −
Diamino t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl Group, 2, 3
-Dicyano t-butyl group, 1,2,3-tricyanopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyano Isopropyl group, 2,
3-dicyano t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-
Nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group,
2,3-dinitro t-butyl group, 1,2,3-trinitropropyl group, nitromethyl group, 1-nitroethyl group,
2-nitroethyl group, 2-nitroisobutyl group, 1,2
-Dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,3-trinitropropyl group, phenyl group, 1-naphthyl group, 2-
Naphthyl group, 1-anthryl group, 2-anthryl group, 9
-Anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-
Naphthacenyl group, 9-naphthacenyl group, 4-styrylphenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-ter Phenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-
Terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p
-T-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group,
4′-methylbiphenylyl group, 4 ″ -t-butyl-p-
Terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group , 5-indolyl group, 6
-Indolyl group, 7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group,
5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group A nyl group, a 2-quinolyl group,
3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6
-Quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-
Isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-
Isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group , 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9 -Phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group,
9-acridinyl group, 1,7-phenanthroline-2-
Yl group, 1,7-phenanthrolin-3-yl group, 1,
7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthroline-6
-Yl group, 1,7-phenanthrolin-8-yl group,
1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl Group, 1,8-phenanthrolin-4-yl group, 1,8-
Phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthroline-9-yl group, 1, 8
-Phenanthroline-10-yl group, 1,9-phenanthrolin-2-yl group, 1,9-phenanthroline-3
-Yl group, 1,9-phenanthrolin-4-yl group,
1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group Group, 1,9-phenanthrolin-10-yl group, 1,1
A 0-phenanthrolin-2-yl group, a 1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-
Phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2, 9
Phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10
-Yl group, 2,8-phenanthrolin-1-yl group,
2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group Group, 2,8-phenanthroline-7-yl group, 2,8-
Phenanthroline-9-yl group, 2,8-phenanthroline-10-yl group, 2,7-phenanthroline-1-
Yl group, 2,7-phenanthrolin-3-yl group, 2,
7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthroline-6
-Yl group, 2,7-phenanthrolin-8-yl group,
2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2
-Phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2- An oxazolyl group, a 4-oxazolyl group,
5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole-5-yl group,
3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-
Methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1- Indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1
-Indolyl group, 4-t-butyl 1-indolyl group, 2
-T-butyl 3-indolyl group, 4-t-butyl 3-indolyl group and the like.

Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group and a t-butyl group.
Butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxy Ethyl group,
1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-
Chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group,
2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group,
1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3
-Trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo t-butyl group, 1,2,
3-tribromopropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromot-butyl Group, 1,
2,3-tribromopropyl group, iodomethyl group, 1-
Iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo t-butyl group,
1,2,3-triiodopropyl group, iodomethyl group,
1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo t-butyl group, 1,2,3-triiodo Propyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3
-Diaminoisopropyl group, 2,3-diamino t-butyl group, 1,2,3-triaminopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-
Aminoisobutyl group, 1,2-diaminoethyl group, 1,
3-diaminoisopropyl group, 2,3-diamino t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,
A cyanoisobutyl group, a 1,2-dicyanoethyl group,
1,3-dicyanoisopropyl group, 2,3-dicyano t
-Butyl group, 1,2,3-tricyanopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano t-butyl group, 1,2,3-tricyanopropyl group,
Nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,3 -Trinitropropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-
Examples thereof include a dinitro t-butyl group and a 1,2,3-trinitropropyl group.

The substituted or unsubstituted alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butanedienyl,
-Methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2- Phenylallyl group, 3
-Phenylallyl group, 3,3-diphenylallyl group,
Examples thereof include a 1,2-dimethylallyl group, a 1-phenyl-1-butenyl group, and a 3-phenyl-1-butenyl group.

Examples of the substituted or unsubstituted cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a 4-methylcyclohexyl group.

A substituted or unsubstituted alkoxy group is represented by-
A group represented by OY, wherein Y is ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n
-Hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-
Dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,
2,3-trihydroxypropyl group, chloromethyl group,
1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloro Propyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3
-Dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2
-Bromoisobutyl group, 1,2-dibromoethyl group,
1,3-dibromoisopropyl group, 2,3-dibromot
-Butyl group, 1,2,3-tribromopropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo t-butyl group, 1,2,3-tribromopropyl group,
Iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo t-butyl group, 1,2,3 -Triiodopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-
T-butyl diiodo, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3 -Diaminoisopropyl group, 2,3
-Diamino t-butyl group, 1,2,3-triaminopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 3-diaminoisopropyl group, 2,
3-diamino t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-
Cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group,
2,3-dicyano t-butyl group, 1,2,3-tricyanopropyl group, cyanomethyl group, 1-cyanoethyl group,
2-cyanoethyl group, 2-cyanoisobutyl group, 1,2
-Dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitro Isobutyl group,
1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,3-
Trinitropropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,
And a 3-trinitropropyl group.

Examples of the substituted or unsubstituted aromatic hydrocarbon group include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, and 1-phenanthryl. , 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9
-Phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-
Pyrenyl group, 4-pyrenyl group, 2-biphenylyl group,
3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl Group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p-
(2-phenylpropyl) phenyl group, 3-methyl-2-
Naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group,
4 ''-t-butyl-p-terphenyl-4-yl group and the like.

The substituted or unsubstituted aromatic heterocyclic group includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl, and 4-pyridinyl. , 1-indolyl group, 2-
Indolyl group, 3-indolyl group, 4-indolyl group,
5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3
-Isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5 -Benzofuranyl group, 6-benzofuranyl group, 7
-Benzofuranyl group, 1-isobenzofuranyl group, 3-
Isobenzofuranyl group, 4-isobenzofuranyl group, 5
-Isobenzofuranyl group, 6-isobenzofuranyl group,
7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3- Isoquinolyl group, 4-isoquinolyl group, 5
-Isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group,
5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group , 3-
Phenanthridinyl group, 4-phenanthridinyl group, 6
-Phenanthridinyl group, 7-phenanthridinyl group,
8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1 , 7-phenanthroline-2-yl group, 1,7-phenanthroline-3
-Yl group, 1,7-phenanthrolin-4-yl group,
1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group Group, 1,7-phenanthrolin-10-yl group, 1,8
-Phenanthroline-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthroline-4-
Yl group, 1,8-phenanthrolin-5-yl group, 1,
8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthroline-9
-Yl group, 1,8-phenanthrolin-10-yl group,
1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl Group, 1,9-phenanthrolin-6-yl group, 1,9-
Phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthroline-10-
An yl group, a 1,10-phenanthrolin-2-yl group,
1,10-phenanthrolin-3-yl group, 1,10-
Phenanthroline-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthroline-1-
Yl group, 2,9-phenanthrolin-3-yl group, 2,
9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthroline-6
-Yl group, 2,9-phenanthrolin-7-yl group,
2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl Group, 2,8-phenanthrolin-4-yl group, 2,8-
Phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2, 8
-Phenanthroline-10-yl group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthroline-3
-Yl group, 2,7-phenanthrolin-4-yl group,
2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group Group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, -Phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group,
4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrole- 3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group,
3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-
t-butylpyrrole-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl Group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group,
4-t-butyl 3-indolyl group, and the like.

The substituted or unsubstituted aralkyl group includes benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthyl Methyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-
α-naphthylisopropyl group, β-naphthylmethyl group,
1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-
Pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromo Benzyl group, o
-Bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-amino Benzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p
-Cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like.

The substituted or unsubstituted aryloxy group is represented by —OZ, where Z is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group,
2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1
-Pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-
Biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl -4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p -(2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t -Butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4
-Pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3
-Isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5 -Benzofuranyl group, 6-benzofuranyl group, 7
-Benzofuranyl group, 1-isobenzofuranyl group, 3-
Isobenzofuranyl group, 4-isobenzofuranyl group, 5
-Isobenzofuranyl group, 6-isobenzofuranyl group,
7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3- Isoquinolyl group, 4-isoquinolyl group, 5
-Isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group,
5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group,
2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9- Phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthroline-2-yl Group, 1,7-phenanthrolin-3-yl group, 1,7-
Phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthroline-8-yl group, 1, 7
-Phenanthroline-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthroline-2
-Yl group, 1,8-phenanthrolin-3-yl group,
1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group Group, 1,8-phenanthrolin-9-yl group, 1,8-
Phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-
Yl group, 1,9-phenanthrolin-4-yl group, 1,
9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthroline-7
-Yl group, 1,9-phenanthroline-8-yl group,
1,9-phenanthrolin-10-yl group, 1,10-
Phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthroline-4
-Yl group, 1,10-phenanthrolin-5-yl group,
2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group Group, 2,9-phenanthrolin-6-yl group, 2,9-
Phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-
Yl group, 2,8-phenanthrolin-1-yl group, 2,
8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthroline-5
-Yl group, 2,8-phenanthrolin-6-yl group,
2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl Group, 2,7-phenanthrolin-3-yl group, 2,7-
Phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2, 7
-Phenanthroline-9-yl group, 2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group , 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl Group, 3-flazanyl group, 2-thienyl group, 3-
Thienyl group, 2-methylpyrrole-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl
Yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrole-5-yl Yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-
Indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group , 4-t-butyl 3-indolyl group and the like.

A substituted or unsubstituted alkoxycarbonyl group is represented by —COOY, wherein Y represents a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group,
s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group,
2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, Chloromethyl group, 1-chloroethyl group, 2-chloroethyl group,
2-chloroisobutyl group, 1,2-dichloroethyl group,
1,3-dichloroisopropyl group, 2,3-dichloro-
t-butyl group, 1,2,3-trichloropropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group , 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1 , 3-dibromoisopropyl group, 2,3-
Dibromo t-butyl group, 1,2,3-tribromopropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl Group, 2, 3
-Dibromo t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodo Isopropyl group, 2,
3-diiodo t-butyl group, 1,2,3-triiodopropyl group, iodomethyl group, 1-iodoethyl group, 2-
Iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group,
2,3-diiodo t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group,
2-aminoethyl group, 2-aminoisobutyl group, 1,2
-Diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino t-butyl group, 1,2,3-triaminopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group,
1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino t-butyl group, 1,2,3-
Triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,
3-tricyanopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl Group, 1,
2,3-tricyanopropyl group, nitromethyl group, 1-
Nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group,
1,2,3-trinitropropyl group, nitromethyl group,
1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,3-trinitro And a propyl group.

Examples of the divalent group forming a ring include:
Tetramethylene group, pentamethylene group, hexamethylene group, diphenylmethane-2,2'-diyl group, diphenylethane-3,3'-diyl group, diphenylpropane-
4,4'-diyl group and the like.

In addition, at least one of the light emitting layer and the laminated film
Another compound specified by the present invention as a material forming a layer
Is a compound having a structure represented by the general formula (2)
You. R¹~ R²⁶At least one of which is -NAr¹Ar
^Two(Ar¹, Ar^TwoAre independently substituted or omitted
Represents an aryl group having 6 to 20 carbon atoms. )
A diarylamino group and other R¹~ R²⁶Each
Independently a hydrogen atom, the above-mentioned halogen atom, hydroxy
Group, the above-mentioned substituted or unsubstituted amino group, nitro
Group, cyano group, the above-mentioned substituted or unsubstituted alkyl
Group, the above-mentioned substituted or unsubstituted alkenyl group,
A substituted or unsubstituted cycloalkyl group,
Or an unsubstituted alkoxy group, the above-mentioned substituted or unsubstituted
A substituted aromatic hydrocarbon group, the above-mentioned substituted or unsubstituted aromatic group
Aromatic heterocyclic group, the above-mentioned substituted or unsubstituted aralkyl
Group, the above-mentioned substituted or unsubstituted aryloxy group,
The substituted or unsubstituted alkoxycarbonyl group,
Represents a ruboxyl group. Also R ¹~ R²⁶Is out of them
And the two may form a ring.

The aryl group having 6 to 20 carbon atoms includes a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a naphthacenyl group, a pyrenyl group and the like. Examples of the substituent of these aryl groups include the above-mentioned halogen atom, hydroxyl group, the above-mentioned substituted or unsubstituted amino group, nitro group, cyano group, the above-mentioned substituted or unsubstituted alkyl group, the above-mentioned substituted or unsubstituted alkyl group. Substituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle Groups, the above-mentioned substituted or unsubstituted aralkyl groups, the above-mentioned substituted or unsubstituted aryloxy groups, the above-mentioned substituted or unsubstituted alkoxycarbonyl groups, and carboxyl groups.

The styryl groups Ar ¹ and Ar ² have as substituents include unsubstituted styryl groups and 2,2-
In addition to the diphenylvinyl group, as a substituent of the terminal phenyl group, the halogen atom, the hydroxyl group, the substituted or unsubstituted amino group, the nitro group, the cyano group, the substituted or unsubstituted alkyl group, A substituted or unsubstituted alkenyl group, the substituted or unsubstituted cycloalkyl group, the substituted or unsubstituted alkoxy group, the substituted or unsubstituted aromatic hydrocarbon group, the substituted or unsubstituted An aromatic heterocyclic group, the substituted or unsubstituted aralkyl group, the substituted or unsubstituted aryloxy group, the substituted or unsubstituted alkoxycarbonyl group, a substituted styryl group having a carboxyl group, or the like; Examples include a 2-diphenylvinyl group.

The following are examples of compounds of the present invention. still,
The present invention is not limited to these. The specific compound specified in the present invention is, for example, a specific compound (3) (tri-9,10-anthrylene) shown in Chemical formula 5, and a specific compound (4) (10-di-p-tolylaminotri-) shown in Chemical formula 6.
9,10-anthrylene), the specific compound (5) shown in Chemical formula 7 (10,10 ''-bis (di-p-tolylamino) tri-9,10-anthrylene), the specific compound (6) shown in Chemical formula 8 10- (N-phenyl-Np- (4-
Methylphenylvinyl) phenylamino) tri-9.1
0-anthrylene), the specific compound (7) (1
0,10 ''-bis (N-phenyl-Np- (4-methylphenylvinyl) phenylamino) tri-9,10
-Anthrylene) and the like.

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The organic EL device according to the present invention has a structure in which one or two or more organic layers are laminated between anode and cathode electrodes, for example, as shown in FIG. As shown in FIG. 2, a stacked structure of an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, a stacked structure of an anode, a light emitting layer, an electron transport layer, and a cathode as shown in FIG. As shown in the figure, a laminated structure of an anode, a hole transport layer, a light emitting layer, and a cathode is provided on a substrate. The compound specified in the present invention may be used in any of the organic layers of the above-mentioned laminated structure, or may be used as a mixture by doping another hole transporting material, a light emitting material, or an electron transporting material.

The material used in the present invention as a material for forming the hole transport layer is not limited to the compound specified in the present invention.
Any compound may be used as long as it is used as a hole transport material. For example, as a hole transport material, the following chemical formula 1
0, bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane (hereinafter referred to as compound [01]
), N, N'-diphenyl-N, N'-bis (3
-Methylphenyl) -1,1'-biphenyl-4,4 '
-Diamine (hereinafter, referred to as compound [02]), N, N
'-Diphenyl-NN-bis (1-naphthyl) -1,
And triphenyldiamines such as 1′-biphenyl) -4,4′-diamine [03], and starburst-type molecules (hereinafter, referred to as compounds [04] to [06]).

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The material used in the present invention as the material for forming the electron transporting layer is not limited to the compound specified in the present invention, but is usually
Any compound may be used as long as it is a compound used as an electron transport material. For example, as an electron transport material,
2- (4-biphenylyl) -5- (4
-T-butylphenyl) -1,3,4-oxadiazole (hereinafter, referred to as compound [07]), bis {2- (4-
t-butylphenyl) -1,3,4-oxadiazole {-m-phenylene (hereinafter, referred to as compound [08])
And quinolinol-based metal complexes (hereinafter, compounds [11] to [1]
4]).

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3. The anode of the organic thin film EL element has a role of injecting holes into the light emitting layer or the hole transport layer.
It is effective to have a work function of 5 eV or more. Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), gold,
Silver, platinum, copper, etc. can be applied. Further, as the cathode, a material having a small work function is preferable for the purpose of injecting electrons into the electron transport layer or the light emitting layer. The cathode material is not particularly limited, but specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-
A silver alloy or the like can be used.

When forming at least one of the light emitting layer or the laminated film with the compound specified in the present invention or the mixture containing the compound, a vacuum evaporation method, a molecular beam evaporation method (MBE)
Or a known method such as a dipping method of a solution in which a compound is dissolved in a solvent, a spin coating method, a casting method, a bar coating method, a roll coating method and the like. When forming a layer of an organic EL element using a material other than the specified compound, the formation method is not particularly limited. For example, a conventionally known vacuum deposition method,
Spin coating can be used. Organic EL of the present invention
The thickness of each organic layer of the device is not particularly limited, but generally, if the thickness is too thin, defects such as pinholes are likely to occur,
On the other hand, if the thickness is too large, a high applied voltage is required and the efficiency is deteriorated.

[0029]

Embodiments of the present invention will be described below in detail with reference to the accompanying drawings. The present invention is not limited by the following examples unless it exceeds the gist.

[0030]

EXAMPLES First, as an example of the compound specified in the present invention,
The synthesis examples of the compound (7) from the compound (3) shown in Chemical formulas 5 to 9 are shown below. Synthesis Example 1-Compound (3) (tri-9,10-anthrile
To synthesize tri-9,10-anthrylene shown in compounds of the synthesis of 5 down) (3), first, generates a 9-lithio-anthracene from 9-bromo-anthracene and lithium, followed by generation of 9-lithio-anthracene And anthraquinone. Next, the obtained product is reductively aromatized with hydrogen iodide and phosphinic acid, and further, according to a conventional method,
Purification yielded the desired tri-9,10-anthrylene.

Synthesis Example 2 Compound (4) (10-di-p-
Synthesis of Compound (4) of 10-di-p -tolylaminotri- ( tolylaminotri-9,10-anthrylene)
To synthesize 9,10-anthrylene, first, 53 g of tri-9,10-anthrylene obtained in Synthesis Example 1 and N-
18 g of bromosuccinimide was put in a flask together with chloroform, and reacted while stirring all day and night. Then
The reaction solution was washed with water, the organic layer was dried, and then purified according to a conventional method to obtain 10-bromotri-9,10-anthrylene. Next, 30 g of 10-bromotri-9,10-anthrylene, 9 g of di-p-tolylamine, 3.5 g of potassium carbonate, and 1.5 g of copper powder were put into a three-necked flask together with nitrobenzene, and stirred at 200 ° C. for 30 hours to react. I let it. After the completion of the reaction, toluene and chloroform were added, followed by filtration to remove inorganic substances. After distilling off toluene and nitrobenzene under reduced pressure, the residue is purified according to a conventional method to obtain the desired 10-di-p-tolylaminotri-9,1.
0-Anthrylene was obtained.

Synthesis Example 3 Compound (5) (10, 10 ″)
-Bis (di-p-tolylamino) tri-9,10-anne
In order to synthesize 10,10 ″ -bis (di-p-tolylamino) tri-9,10-anthrylene, compound (5 ) of Synthesis 7), first, tri-9,10-anthrylene obtained in Synthesis Example 1 was synthesized. 53 g of 10-anthrylene and 36 g of N-bromosuccinimide were put in a flask together with chloroform, and reacted while stirring all day and night. Next, the reaction solution was washed with water, the organic layer was dried, and then purified according to a conventional method to obtain 10,10 ″ -dibromotri-9,10-anthrylene. Then, 1
35 g of 0,10 ″ -dibromotri-9,10-anthrylene, 18 g of di-p-tolylamine, 7 g of potassium carbonate
g and 3 g of copper powder were placed in a three-necked flask together with nitrobenzene, and reacted by stirring at 200 ° C. for 30 hours. After the completion of the reaction, toluene and chloroform were added, followed by filtration to remove inorganic substances. After distilling off toluene and nitrobenzene under reduced pressure, the product is purified according to a conventional method to obtain the desired 1
0,10 ''-bis (di-p-tolylamino) tri-
9,10-Anthrylene was obtained.

Synthesis Example 4 Compound (6) (10- (N-F
Phenyl-Np- (4-methylphenylvinyl) phenyl
(6) 10- (N-phenyl -Np-) -( amino) tri-9,10-anthrylene)
(4-methylphenylvinyl) phenylamino) tri-
To synthesize 9,10-anthrylene, first, di-p
N-phenyl-Np- instead of 9 g of tolylamine
Synthesis Example 2 except that 8.5 g of tolylamine was used.
In the same manner as described above, 10- (N-phenyl-Np-tolylamino) tri-9,10-anthrylene was obtained. Then, 10- (N-phenyl-Np-tolylamino) tri-9,10-anthrylene was dissolved in toluene, phosphorus oxychloride was added thereto, the mixture was stirred at room temperature, and N-methylformanilide was further added thereto. The mixture was added dropwise and stirred at 50 ° C. for 5 hours to react. After completion of the reaction, the mixture was slowly poured into cold water, transferred to a separating funnel, and washed several times with water until the toluene layer became neutral. Subsequently, after drying over magnesium sulfate, the solvent was distilled off and 10- (Np-formylphenyl-N-
Tolylamino) tri-9,10-anthrylene was synthesized. Next, diethyl 4-methylbenzylphosphonate and sodium hydride were added to dimethyl sulfoxide, and a stirred solution of 10- (Np-formylphenyl-N-tolylamino) tri-9,10-anthrylene in dimethyl sulfoxide was added dropwise. Then, the mixture was reacted by stirring at 50 ° C. for 3 hours. After completion of the reaction, the reaction solution was poured into ice water, neutralized by adding an acid, and extracted with ethyl acetate. After the solvent was removed under reduced pressure, purification was carried out according to a conventional method to obtain the desired 10- (N-phenyl-NP- (4-methylphenylvinyl) phenylamino) tri-9,10-anthrylene.

Synthesis Example 5 Compound (7) (10, 10 ″)
-Bis (N-phenyl-Np- (4-methylphenyl
Vinyl) phenylamino) tri-9,10-anthrile
In order to synthesize 10,10 ″ -bis (N-phenyl-NP- (4-methylphenylvinyl) phenylamino) tri-9,10-anthrylene,
First, 10,10 ″ -bis (N
-Phenyl-Np-tolylamino) tri-9,10-
You got anthrylene. Then, 10,10 ″ -bis (N-phenyl-Np-tolylamino) tri-9,1
0-Anthrylene was dissolved in toluene, phosphorus oxychloride was added thereto, the mixture was stirred at room temperature, N-methylformanilide was added dropwise thereto, and the mixture was stirred and reacted at 50 ° C. for 5 hours.

After completion of the reaction, the mixture was slowly poured into cold water, transferred to a separating funnel, and washed several times with water until the toluene layer became neutral. Further, after drying with magnesium sulfate, the solvent was distilled off, and 10,10 ″ -bis (Np-formylphenyl-
(N-Tolylamino) tri-9,10-anthrylene was synthesized. Next, diethyl 4-methylbenzylphosphonate and sodium hydride were added to dimethyl sulfoxide,
A solution of 10,10 ″ -bis (Np-formylphenyl-N-tolylamino) tri-9,10-anthrylene in dimethyl sulfoxide was added dropwise to the stirred mixture, and the mixture was stirred at 50 ° C. for 3 hours to react. After completion of the reaction, the reaction solution was poured into ice water, neutralized by adding an acid, and extracted with ethyl acetate.
After the solvent was removed under reduced pressure, the residue was purified according to a conventional method to obtain the desired 10,10 ″ -bis (N-phenyl-Np- (4-
Methylphenylvinyl) phenylamino) tri-9.1
0-Anthrylene was obtained.

Hereinafter, the embodiments of the present invention will be described specifically and in detail by giving examples of organic EL devices using the compounds specified in the present invention as examples. Examples 1 to 11
In Examples 12 to 17, the compounds containing the compounds specified in the present invention were used in the light-emitting layers of Examples 18 to 21.
In Example 2, the compound specified by the present invention is used for the hole transport layer, and in Example 22, the compound specified by the present invention is used for the electron transport layer. Example 1 This example is an example of the organic EL device according to the present invention, and FIG. 1 is a cross-sectional view showing the layer structure of the organic EL device of Example 1. As shown in FIG. 1, the organic EL element 10 of this embodiment includes a glass substrate 1, and a laminated film including the anode 2, the light emitting layer 4, and the cathode 6 formed on the glass substrate 1. . In order to form the organic EL element 10 of this embodiment, an anode 2 was formed by sputtering ITO on a glass substrate 1 so that the sheet resistance became 20 Ω / □. Next, on the anode 2, a film made of the specific compound (3) represented by Chemical Formula 5 was deposited to a thickness of 40 nm by a vacuum evaporation method to form a light emitting layer 4. Next, a magnesium-silver alloy was deposited to a thickness of 200 nm by a vacuum evaporation method to form the cathode 6, and the organic EL device 10 of this example was manufactured. Organic EL device 1 obtained
When a direct current voltage of 5 V was applied to 0, the luminance was 90 cd / m
² luminescence was obtained.

Embodiment 2 This embodiment is another embodiment of the organic EL device according to the present invention. The same configuration as that of the organic EL device 10 was provided, and the device was manufactured in the same manner as in Example 1. Organic EL obtained
When a DC voltage of 5 V was applied to the device, the luminance was 250 cd.
/ M ² was obtained.

Example 3 This example is still another example of the organic EL device according to the present invention. The organic EL device 10 was manufactured in the same manner as in Example 1 with the same configuration as that of the organic EL device 10 of Example 1. When a DC voltage of 5 V was applied to the obtained organic EL device, the luminance was 300
Light emission of cd / m ² was obtained.

Example 4 This example is still another example of the organic EL device according to the present invention. The organic EL device 10 was manufactured in the same manner as in Example 1 with the same configuration as that of the organic EL device 10 of Example 1. When a DC voltage of 5 V was applied to the obtained organic EL device, the luminance was 480.
Light emission of cd / m ² was obtained.

Example 5 This example is still another example of the organic EL device according to the present invention. The organic EL device 10 was manufactured in the same manner as in Example 1 with the same configuration as that of the organic EL device 10 of Example 1. When a DC voltage of 5 V was applied to the obtained organic EL device, the luminance was 600
Light emission of cd / m ² was obtained.

Embodiment 6 This embodiment is still another embodiment of the organic EL device according to the present invention, and has a film thickness of 40 nm on the anode 2 by a spin coating method using a chloroform solution of the specific compound (7). Except that the light-emitting layer 4 was formed, the same configuration as that of the organic EL element 10 of Example 1 was provided, and the device was manufactured in the same manner as Example 1. When a DC voltage of 5 V was applied to the obtained organic EL device, light emission with a luminance of 210 cd / m ² was obtained.

Embodiment 7 This embodiment is still another embodiment of the organic EL device according to the present invention. FIG. 2 is a sectional view showing the layer structure of the organic EL device of Embodiment 7. As shown in FIG. 2, the organic EL device 20 of this embodiment includes a glass substrate 21, an anode 22, a hole transport layer 23, a light emitting layer 24, an electron transport layer 25, and a cathode formed on the glass substrate 1. 26. In order to form the organic EL element 20 of this example, ITO was formed on a glass substrate 21 by sputtering so that the sheet resistance became 20 Ω / □, and the anode 22 was formed. Then, on the anode 22, N, N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,
1′-biphenyl] -4,4′-diamine (compound [0
2]) was deposited to a thickness of 50 nm by a vacuum evaporation method to form a hole transport layer 23. Next, the specific compound (3) is deposited on the hole transport layer 23 by a vacuum evaporation method to a thickness of 40 nm to form the light emitting layer 2.
4 was formed. Further, on the light emitting layer 24, 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,
Electron transport layer 25 was formed by depositing 3,4-oxadiazole (compound [07]) to a thickness of 20 nm by a vacuum evaporation method. Next, a magnesium-silver alloy was deposited to a thickness of 200 nm by a vacuum evaporation method to form a cathode, and an organic EL device 20 of Example 7 was produced. When a DC voltage of 10 V was applied to the obtained organic EL device 20, light emission with a luminance of 920 cd / m ² was obtained.

Example 8 This example is still another example of the organic EL device according to the present invention. 7 was provided in the same manner as in the organic EL element 20 of Example 7, and was manufactured in the same manner as in Example 7. When a DC voltage of 10 V was applied to the obtained organic EL device 20, light emission with a luminance of 3000 cd / m ² was obtained.

Embodiment 9 This embodiment is another embodiment of the organic EL device according to the present invention.
NN-bis (1-naphthyl) -1,1′-biphenyl) -4,4′-diamine (compound [03]) is used to convert the electron transport layer 25 to bis {2- (4-t-butylphenyl) −
Except that it was formed of 1,3,4-oxadiazole} -m-phenylene (compound [08]), it had the same configuration as the organic EL element 20 of Example 7 and was manufactured in the same manner as Example 7. did. A DC voltage of 10 V is applied to the obtained organic EL device 20.
Upon application, light emission with a luminance of 1200 cd / m ² was obtained.

Example 10 This example is still another example of the organic EL device according to the present invention. And the organic EL of Example 7 except that the electron transport layer 25 was formed of the compound [11].
The device has the same configuration as that of the element 20 and is manufactured in the same manner as in Example 7. When a DC voltage of 10 V was applied to the obtained organic EL device 20, light emission with a luminance of 3400 cd / m ² was obtained.

Embodiment 11 This embodiment is another embodiment of the organic EL device according to the present invention, in which the hole transport layer 23 is made of the compound [05] and the light emitting layer 24 is made of the specific compound (7). And the organic EL of Example 7 except that the electron transport layer 25 was formed of the compound [12].
The device has the same configuration as that of the element 20 and is manufactured in the same manner as in Example 7. When a DC voltage of 10 V was applied to the obtained organic EL device 20, light emission with a luminance of 4500 cd / m ² was obtained.

Embodiment 12 This embodiment is still another embodiment of the organic EL device according to the present invention. FIG. 3 is a sectional view showing the layer structure of the organic EL device of Embodiment 12. The organic EL element 30 of the present embodiment
As shown in FIG. 3, a glass substrate 31, an anode 32 formed on the glass substrate 1, a light emitting layer 34, an electron transport layer 35,
And a laminated film including the cathode 36.
In order to form the organic EL element 30 of this embodiment, ITO was formed on a glass substrate 31 by sputtering so that the sheet resistance became 20 Ω / □, and the anode 32 was formed. Then, on the anode 32, N, N'-diphenyl-NN-bis (1-naphthyl) -1,1'-biphenyl) -4,4
'-Diamine (compound [03]) and the specific compound (3) were co-evaporated at a weight ratio of 1:10 to form a light emitting layer 34 having a thickness of 50 nm. Next, on the light emitting layer 34, the compound [0
[9] was deposited by a vacuum evaporation method to a thickness of 50 nm to form an electron transport layer. Subsequently, a 200 nm-thick magnesium-silver alloy was deposited on the electron transport layer 35 to form a cathode 36, thereby manufacturing an organic EL device 30 of Example 12. When a DC voltage of 10 V was applied to the obtained organic EL device 30, light emission with a luminance of 900 cd / m ² was obtained.

Example 13 This example is still another example of the organic EL device according to the present invention. Having the same configuration as that of the organic EL element 30 of Example 12 except that
It was produced in the same manner as in Example 12. Organic EL device 3 obtained
When a DC voltage of 10 V was applied to 0, the luminance was 2300 c.
Light emission of d / m ² was obtained.

Example 14 This example is still another example of the organic EL device according to the present invention, in which the specific compound (7) and N, N
'-Diphenyl-NN-bis (1-naphthyl) -1,
1′-biphenyl) -4,4′-diamine (compound [0
3]) was formed by a spin coating method using a chloroform solution containing a molar ratio of 1:10 to form a light-emitting layer 34 having a thickness of 40 nm. Except that the organic EL device 30 of Example 1 was used,
It was produced in the same manner as in Example 2. When a DC voltage of 10 V was applied to the obtained organic EL device 30, light emission with a luminance of 900 cd / m ² was obtained.

Embodiment 15 This embodiment is still another embodiment of the organic EL device according to the present invention. FIG. 4 is a sectional view showing the layer structure of the organic EL device of Embodiment 15. The organic EL element 40 of the present embodiment
As shown in FIG. 3, a glass substrate 41, an anode 42 formed on the glass substrate 1, a hole transport layer 43, a light emitting layer 44,
And a laminated film including the cathode 46.
In order to form the organic EL device 30 of this example, ITO was formed on a glass substrate 41 by sputtering so that the sheet resistance became 20 Ω / □, and the anode 42 was formed. Then, on the anode 42, N, N'-diphenyl-NN-bis (1-naphthyl) -1,1'-biphenyl) -4,4
'-Diamine (compound [03]) was deposited to a thickness of 50 nm by a vacuum evaporation method to form a hole transport layer 43. Next, the compound [11] and the specific compound (3) were co-deposited in a vacuum at a weight ratio of 20: 1 to form the light emitting layer 44 having a thickness of 50 nm. Subsequently, a cathode 46 was formed by depositing a 200 nm-thick magnesium-silver alloy, and the organic EL element 40 of this embodiment was formed.
Was prepared. A DC voltage of 10 V is applied to the obtained organic EL element 40.
Upon application, light emission with a luminance of 1100 cd / m ² was obtained.

Example 16 This example is still another example of the organic EL device according to the present invention, wherein the compound [11] and the specific compound (5) were used as the light emitting layer 44 at a weight ratio of 20: 1. Except for using a 50 nm-thick film co-deposited in vacuum at a ratio, the organic EL element 40 of Example 15 was provided with the same configuration, and was manufactured in the same manner as Example 15. A DC voltage of 1 is applied to the obtained organic EL element 40.
When 0 V was applied, light emission with a luminance of 1800 cd / m ² was obtained.

Embodiment 17 This embodiment is still another embodiment of the organic EL device according to the present invention, in which the hole transport layer 43 is formed of N, N'-diphenyl-
N, N'-bis (3-methylphenyl)-[1,1'-
Biphenyl] -4,4'-diamine (compound [02])
And the organic EL device of Example 15 except that a film obtained by vacuum co-evaporation of the compound [13] and the specific compound (7) at a weight ratio of 20: 1 was used as the light emitting layer 44. 40
The same configuration as that of Example 15 was provided, and it was manufactured in the same manner as in Example 15.
When a DC voltage of 10 V was applied to the obtained organic EL device 40, light emission with a luminance of 2300 cd / m ² was obtained.

Example 18 This example is still another example of the organic EL device according to the present invention. Except that each was formed, the same configuration as the organic EL element 20 of Example 7 was provided,
It was produced in the same manner as in Example 7. Organic EL device 20 obtained
When a DC voltage of 10 V is applied, the luminance is 850 cd /
m ² emission was obtained.

Example 19 This example is still another example of the organic EL device according to the present invention, except that the hole transport layer 23 was formed of the specific compound (5). The same configuration as that of the organic EL element 20 was provided, and it was manufactured in the same manner as in Example 18. When a DC voltage of 10 V was applied to the obtained organic EL device 20, light emission with a luminance of 1300 cd / m ² was obtained.

Example 20 This example is still another example of the organic EL device according to the present invention, except that the hole transport layer 23 was formed of the specific compound (6). The same configuration as that of the organic EL element 20 was provided, and it was manufactured in the same manner as in Example 18. When a DC voltage of 10 V was applied to the obtained organic EL device 20, light emission with a luminance of 1500 cd / m ² was obtained.

Example 21 This example is still another example of the organic EL device according to the present invention. The same configuration as that of the organic EL element 20 was provided, and it was manufactured in the same manner as in Example 18. When a DC voltage of 10 V was applied to the obtained organic EL device 20, light emission with a luminance of 1800 cd / m ² was obtained.

Example 22 This example is still another example of the organic EL device according to the present invention, in which the hole transport layer 23 is formed of N, N'-diphenyl-
N-N-bis (1-naphthyl) -1,1′-biphenyl) -4,4′-diamine (compound [03]), the light-emitting layer 24 is a compound [13], and the electron transport layer 25 is a specific compound. Except that they were formed in (3), respectively, they had the same configuration as the organic EL element 20 of Example 7, and were manufactured in the same manner as Example 7. A DC voltage of 10 is applied to the obtained organic EL device 20.
When V was applied, light emission with a luminance of 980 cd / m ² was obtained.

In Examples 1 to 6, in which a direct current voltage of 5 V was applied to the organic EL device to examine the light emission characteristics, the specific compound (7) was used.
In Example 7 to Example 22, in which the luminance was the highest in the organic EL device of Example 5 using, and the light emitting characteristics were examined by applying a DC voltage of 10 V to the organic EL device, the light emitting layer formed of the specific compound (7) was used. Example 11 sandwiched between a hole transport layer and an electron transport layer
Has the highest luminance. This indicates that the specific compound (7) is extremely effective in improving the emission specification.

[0059]

According to the present invention, there is provided an organic electroluminescence device having a light-emitting layer or a laminated film comprising a light-emitting layer and at least one other organic thin film layer between an anode and a cathode. Alternatively, by forming at least one layer of the laminated film with the compound specified in the present invention or a mixture containing the compound, an organic electroluminescence element having higher luminance emission characteristics than before can be realized.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view illustrating a layer structure of an organic EL element of Examples 1 to 6.

FIG. 2 shows Embodiments 7 to 11 and Embodiments 18 to 2
FIG. 4 is a cross-sectional view illustrating a layer structure of an organic EL element of No. 2.

FIG. 3 is a cross-sectional view illustrating a layer structure of an organic EL element of Examples 12 to 14.

FIG. 4 is a cross-sectional view illustrating a layer structure of an organic EL element of Examples 15 to 17.

[Explanation of symbols]

10, 20, 30, 40 Organic electroluminescence device 1, 21, 31, 41 Substrate 2, 22, 32, 42 Anode 23, 43 Hole transport layer 4, 24, 34, 44 Light emitting layer 25, 35 Electron transport layer 6 , 26,36,46 cathode

Claims (9)

[Claims] 1. An organic electroluminescent device having one or more organic thin film layers including a light emitting layer between an anode and a cathode, wherein at least one of the organic thin film layers is made of a material represented by the following general formula (1) alone. Alternatively, an organic electroluminescence device, which is contained as a mixture. Embedded image (Wherein, R ^{1 to} R ²⁶ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted Alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group , A substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group, and two of R ^{1 to} R ²⁶ may form a ring. 2. An organic electroluminescence device having one or more organic thin film layers including a light emitting layer between an anode and a cathode, wherein at least one of the organic thin film layers is made of a material represented by the following general formula (2) alone. Alternatively, an organic electroluminescence device, which is contained as a mixture. Embedded image (Wherein, R ^{1 to} R ²⁶ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted Alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group Or a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group, and two of R ^{1 to} R ²⁶ may form a ring. R
¹ at least one of to R ²⁶ are -NAr ¹ Ar ² (A
r ¹ and Ar ² each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. ) Is a diarylamino group. ) 3. An organic electroluminescence device having one or more organic thin film layers including a light emitting layer between an anode and a cathode, wherein at least one of the organic thin film layers is a compound represented by the general formula (2): An organic electroluminescence device comprising a material in which at least one of Ar ¹ and Ar ² in at least one —NAr ¹ Ar ² group has a substituted or unsubstituted styryl group as a substituent, alone or as a mixture. 4. The organic material according to claim 1, wherein the organic thin film layer has at least a hole transport layer, and this layer contains the compound represented by the general formula (1) alone or as a mixture. Electroluminescence element. 5. The organic material according to claim 2, wherein the organic thin film layer has at least a hole transport layer, and this layer contains the compound represented by the general formula (2) alone or as a mixture. Electroluminescence element. 6. The organic thin film layer has at least a hole transporting layer, and this layer is a compound represented by the general formula (2), wherein at least one of the compounds represented by the general formula (2) is represented by Ar in one —NAr ¹ Ar ² group.
4. The organic electroluminescent device according to claim 3, wherein a material in which at least one of the ¹ , ² groups has a styryl group as a substituent is contained alone or as a mixture. 7. The organic electroluminescent device according to claim 1, wherein the organic thin film layer has at least an electron transport layer, and this layer contains the compound represented by the general formula (1) alone or as a mixture. Luminescent element. 8. The organic electroluminescent device according to claim 2, wherein the organic thin film layer has at least an electron transport layer, and this layer contains the compound represented by the general formula (2) alone or as a mixture. Luminescent element. 9. The organic thin film layer has at least an electron transporting layer, and this layer is a compound represented by the general formula (2), wherein at least one of the compounds represented by the general formula (2) includes Ar in one —NAr ¹ Ar ² group.
4. The organic electroluminescent device according to claim 3, wherein a material in which at least one of the ¹ , ² groups has a styryl group as a substituent is contained alone or as a mixture.